Epichlorohydrin → HCID 86749231, compound

HRID 1586157Notes

Reaction equation

HRID 1586157 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:16][CH2:17][CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][C:12]([OH:24])=[CH:11][CH:10]=3)[CH3:2].[OH-].[K+].[CH2:27]([CH:29]1[O:31][CH2:30]1)Cl>CS(C)=O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:16][CH2:17][CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][C:12]([O:24][CH2:27][CH:29]1[O:31][CH2:30]1)=[CH:11][CH:10]=3)[CH3:2]

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 14797Potassium HydroxideHCID 9818690HCID 9818690, compound

Product 1

HCID 86749231HCID 86749231, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 1-ethyl-6-hydroxy-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine (2 g), DMSO (30 ml) and KOH (2 g) is stirred at room temperature for 0.5 hours, then epichlorohydrin (0.49 ml) is added, and the mixture is stirred overnight. The reaction mixture is partitioned between CH2Cl2 and water, and then the CH2Cl2 layer is separated and evaporated. The residue is purified by column chromatography on silica gel eluting with ethyl acetate to afford the product that is combined with the product from a similar experimental. The combined material is purified further by column chromatography on silica gel eluting with 90% ether/t-butylmethylether, followed by crystallization from ether, to afford 1-ethyl-6-(2,3-epoxypropoxy)-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4amine, m.p. 168°-170° C.

Workup

  1. stirringthe mixture is stirred overnight
  2. customThe reaction mixture is partitioned between CH2Cl2 and water
  3. customthe CH2Cl2 layer is separated
  4. customevaporated
  5. customThe residue is purified by column chromatography on silica gel eluting with ethyl acetate
  6. customto afford the product that
  7. customThe combined material is purified further by column chromatography on silica gel eluting with 90% ether/t-butylmethylether
  8. customfollowed by crystallization from ether

Sources & evidence

ORD record
ord-78f48aeba1f64a0d8f6225441461db1b
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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